About Claire’s Holiday

My story is a familiar one. I woke up one day and realized I needed to be more intentional with the things that bring me joy. It’s different for everyone. For some, it’s raising children, for others, it’s working on their vegetable garden.

For me, it’s discovering new adventures (and connecting with people), in the form of travel.

As each year went by, however, the frequency of trips became fewer, and I found myself consumed with the daily grind of work, and just… life. My reality was stressful, unhappy and anxiety-filled, simply because that’s how I had unknowingly made it.

I wanted to get back to the basics, so, I decided to travel more often.

This blog is an on-going log of my new travel adventures in 2017 (and beyond), where I traveled at least once a month.

My goal for 2017 and beyond

I was like most people, stuck in a busy career and consumed with the everyday stresses caused by work, life, and eventually the big question of what will I do with my life?

The more I thought about it, the more I knew I wanted to travel. And when I say travel, I’m not talking about one that’s attached to approval from a manager, or the typical 2 weeks-out-of-the-year-travel. I’m talking about traveling every single month.

I deliberately made this my goal for 2017, and even though I didn’t know how I would do it, I told myself I would travel and learn new things (including snowboarding), cultures, meet new people, and expand my capacity for growth as a human.

Kissed my 9-5 goodbye

The first thing I did was figure out how I would quit my full-time employment. While I loved the people I worked with, and the company I worked for, it wasn’t realistic for me to travel as much as I wanted, even though I would be working while traveling. I don’t care how cool your boss is, this just won’t happen if you’re expected to be in the office full-time.

So I started looking for contract positions that would allow me flexibility to be remote, and as luck would have it, the travel gods were on my side. I found a contract job, and was lucky enough to be able to stay on with my last company as a remote consultant.

From there, I hustled and networked, and landed a few more awesome clients that allowed me to finally be out of the office for good. This took 4 months, but in the meantime, I booked trips to Seattle, Ireland and Alaska. I wanted to travel no matter what.

I also started my own company in the process, mostly for tax reasons, but also because I wanted to make it official that I’m finally flying free.

Work while travel, it can be done

My next challenge I faced was fine tuning the act of balancing work while traveling. How do you see a new city and get your projects done? I decided to read up and learn every single productivity and focused-based method to enhance my concentration levels and get more done in less time.

This is still a work in progress, but I learned how to balance sightseeing and traveling with working (it involves lots of planning on my Google calendar and queuing up places I want to see in the city I’m in, instead of aimlessly walking around).

At this point, I booked more trips, and went to NYC and tacked on a trip to Montauk, Montreal, along with New Orleans and in December and January, I’ll be in Australia and New Zealand.

I’ll continue filling up these pages with new adventures, so stay tuned…